Themed collection Editor’s Collection
Approaches for peptide and protein cyclisation
Polypeptide cyclisation can enhance thermal stability, proteolytic resistance and membrane permeability. Cyclisation can be achieved by methods including chemical, enzyme and protein tag approaches. Each has strengths and limitations.
Tris(pentafluorophenyl)borane catalyzed C–C and C–heteroatom bond formation
This review showcases a collective depiction on the potential utility of BCF as a versatile catalyst to develop various synthetic transformations.
Recent advances in single-benzene-based fluorophores: physicochemical properties and applications
The recently reported physicochemical properties and applications of single-benzene-based fluorophores (SBBFs) are summarized.
Recent advances in the direct O-arylation of carbohydrates
An emerging approach for the synthesis of O-aryl glycosides and carbohydrate-derived aryl ethers via C(sp2)–O bond formation is reviewed.
Beyond osmium: progress in 1,2-amino oxygenation of alkenes, 1,3-dienes, alkynes, and allenes
Olefin 1,2-difunctionalization is a popular synthetic strategy for synthesis of vicinal amino alcohols and their derivatives. This comprehensive review covers methods developed beyond the pioneering osmium-catalyzed Sharpless amino hydroxylation.
Integrating abiotic chemical catalysis and enzymatic catalysis in living cells
We review hybrid systems of abiotic catalysis and enzymatic catalysis, which function in living cells. This research direction will stimulate multidisciplinary fields, including complex molecule synthesis, energy production, and life science.
Cobalt-catalyzed carbonylation of the C–H bond
Direct carbonylation of the C–H bond is a great tool for installing a carbonyl group in a wide variety of substrates.
Synthetic approaches and applications of sulfonimidates
This review encompasses the developments in sulfonimidate chemistry, focusing on both syntheses and applications of these important organosulfur(VI) species.
Rational design of small molecule fluorescent probes for biological applications
Guidelines based on photophysical tuning, reactivity, isomerization, and energy transfer for rational design of synthetic fluorescent probes for biological systems.
The curious yellow colouring matter of the Iceland poppy
This account provides an chronological overview of the fascinating history of the pigment responsible for the yellow colour of the Iceland poppy (Papaver nudicaule).
Chemical methods for modification of proteins
The field of protein bioconjugation draws attention from stakeholders in chemistry, biology, and medicine. This review provides an overview of the present status, challenges, and opportunities for organic chemists.
Deuteration of terminal alkynes realizes simultaneous live cell Raman imaging of similar alkyne-tagged biomolecules
Two-color Raman imaging of D-alkynes and H-alkynes makes it possible to distinguish and observe similar small molecules in live cells.
Calixarene-decorated liposomes for intracellular cargo delivery
Liposomes equipped at the outer membrane with positively charged calixarenes show improved efficiency in cargo delivery. This is facilitated by the interaction between the macrocycle units and heparan sulfate proteoglycans surrounding the cell.
Chalcogen bonding mediates the formation of supramolecular helices of azapeptides in crystals
Supramolecular M- and P-helices are formed via intermolecular S⋯S and S⋯O chalcogen bonding of alanine-based azapeptides containing a β-turn structure and equipped with a thiophene group at the N- or C-terminus, respectively.
Water binding stabilizes stacked conformations of ferrocene containing sheet-like aromatic oligoamides
The encapsulation of discrete water molecules in flexible sheet-like aromatic oligoamide foldamers, as evidenced by structural and spectroscopic studies, stabilizes their structure.
Plasma induced acceleration and selectivity in strain-promoted azide–alkyne cycloadditions
We report the unexpected acceleration of strain-promoted azide–alkyne cycloaddition in human plasma compared to classical solvent systems. Besides fast kinetics, human plasma also allows for discrimination between two azides in competition reaction.
Mannich-type allylic C–H functionalization of enol silyl ethers under photoredox–thiol hybrid catalysis
The synergy of an Ir-based photosensitizer with mild oxidizing ability and a thiol catalyst enables efficient allylic C–H functionalization of enol silyl ethers with imines under visible light irradiation.
Chemoselective activation of ethyl vs. phenyl thioglycosides: one-pot synthesis of oligosaccharides
Ethyl thioglycosides could be selectively activated in the presence of phenyl thioglycosides carrying the same or even more armed protecting group pattern.
Hydroquinone and benzoquinone-catalyzed aqueous Knoevenagel condensation
Aqueous Knoevenagel condensation of various aldehydes with malononitrile could efficiently proceed using hydroquinone and benzoquinone as mixed catalysts.
Disulphide-mediated site-directed modification of proteins
Site-directed addition of a single thiols handle to proteins by means of temporary disulphide rebridging of solvent exposed disulphides is obtained with a new labelling reagent.
Site-selective modification of proteins using cucurbituril as supramolecular protection for N-terminal aromatic amino acids
Supramolecular protection of N-terminal aromatic amino acids through complexation with cucurbituril can enable site-selective protein modification of unfavored motifs.
Rapid sodium periodate cleavage of an unnatural amino acid enables unmasking of a highly reactive α-oxo aldehyde for protein bioconjugation
A genetically incorporated ThrK unnatural amino acid can undergo rapid periodate oxidation to reveal a reactive internal α-oxo aldehyde.
Hierarchical self-assembly of an azobenzene dyad with inverted amide connection into toroidal and tubular nanostructures
Inversion of the amide connectivity of an azobenzene dyad, which self-assembles into chiral toroids and nanotubes, improves the thermal stability of the assemblies, however it negatively affects supramolecular chirality.
A supramolecular host for phosphatidylglycerol (PG) lipids with antibacterial activity
Various small molecules containing boronic acid and urea functionalities are shown to bind selectively to the bacterial lipid PG (phosphatidylglycerol) and exert antibacterial activity through a membrane-related mechanism.
Duplex vs. folding: tuning the self-assembly of synthetic recognition-encoded aniline oligomers
We present a strategy for characterising and preventing the undesired folding between adjacent units in duplex-forming synthetic hetero-oligomers.
An air-stable, Zn2+-based catalyst for hydrosilylation of alkenes and alkynes
An air-stable, Zn2+-based catalyst for catalytic hydrosilylation reactions of alkenes and alkynes.
Hydrated metal ion as a general acid in the catalytic mechanism of the 8–17 DNAzyme
pH-Rate profiles indicate hydrated M2+ as a general acid in the catalytic mechanism of the RNA-cleaving 8–17 DNAzyme.
The effect of deoxyfluorination and O-acylation on the cytotoxicity of N-acetyl-D-gluco- and D-galactosamine hemiacetals
Multiple deoxyfluorination of GlcNAc/GalNAc hemiacetals generated cytotoxic compounds.
Development of functionalized peptides for efficient inhibition of myostatin by selective photooxygenation
Functionalized peptides which consist of myostatin-binding peptide and on/off-switchable catalyst efficiently inhibit myostatin by selective photooxygenation, leading to a therapeutic strategy for muscular atrophic disorders.
DNAzymes for amine and peptide lysine acylation
In vitro selection identifies DNAzymes that acylate amino groups, including Lys in tethered peptides, and in some cases by transfer of a small glutaryl group.
Post-synthetic transamination at position N4 of cytosine in oligonucleotides assembled with routinely used phosphoramidites
A novel strategy for the efficient and cheap post-modification of oligonucleotides at internal position.
Facile synthesis of sulfotyrosine-containing α-conotoxins
A one-pot neopentyl deprotection and oxidative disulfide pairing strategy was developed for the facile synthesis of sulfotyrosine (sY)-containing α-conotoxins (Ctx).
Revisiting the role of acids and hydrogen bond acceptors in enamine formation
A systematic investigation into the effects of acids and hydrogen bond acceptors on the reaction rates and equilibria of enamine formation is reported.
Absolute handedness control of oligoamide double helices by chiral oxazolylaniline induction
Aromatic oligoamide double helices bearing a chiral oxazolylaniline moiety were synthesized and their helix handedness was completely controlled (de > 99%).
Decomplexation as a rate limitation in the thiol-Michael addition of N-acrylamides
Experimental and computational agreement highlights rate-limiting “product decomplexation” and functional group effects in the thiol-Michael addition, utilized for sequence-defined oligomers.
Photochemical [2 + 2] cycloaddition reaction of carbonyl compounds with Danishefsky diene
An efficient oxetane formation has been developed in the photochemical [2 + 2] cycloaddition reaction of benzophenone with Danishefsky diene.
Tuning activation and self-immolative properties of the bioorthogonal alkene–azide click-and-release strategy
Combinations of aryl azides and trans-cyclooctenes have been studied in a bioorthogonal click-and-release strategy, with two reaction pairings rapidly releasing phenol at micromolar concentrations.
One-pot synthesis of porphyrin-based rotaxanes
Rotaxanes prepared in a one-pot reaction via simultaneous threading-followed-by-stoppering and condensation can be used to generate different co-conformational states making these systems potential multi-state switches.